Lithium diisopropylamide → (5-Chlorobenzofuran-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

99 (25.7 g, 85.1 mmol) is dissolved in 300 ml of tetrahydrofurane and cooled to −78° C. A 2M solution of LDA in THF (93.7 ml, 187.4 mmol) is added dropwise within 45 min. The reaction mixture is allow to warmup to room temperature within 17 h. Then the reaction mixture is quenched with saturated aqueous ammonium chloride solution and evaporated under reduced pressure. The residue is diluted with ethyl acetate, washed with water and brine and dried over sodium sulfate. Evaporation gave 17.2 g of an brown resin which is further purified by flash-chromatography (silicagel, ethyl acetate/hexanes 2:8).

Provenance & Evidence